At what point should you hire a tax professional instead of DIY filing?

Thanks for the reply! Do you think I should look for a CPA specifically or would an enrolled agent be sufficient? And is this something I need year-round or just during tax season?

For your situation, either a CPA or an Enrolled Agent would be fine - EAs specialize specifically in taxation and often charge less than CPAs. The key is finding someone with experience in self-employment and real estate. While most people only need help during tax season, having a brief mid-year check-in can be valuable when you have a side business. This helps ensure you're tracking everything correctly and making appropriate quarterly estimated tax payments if needed.

How exactly does it work? Is it just another tax software or does it actually connect you with tax professionals? I'm also considering getting help but don't want to pay hundreds for a CPA.

Does it handle state taxes too? I live in a state with some weird rules about home office deductions that don't match the federal guidelines.

It's not another tax software - it actually reviews your tax documents and identifies potential issues or opportunities you might miss. You upload your tax docs and it does an AI analysis with human review for accuracy. Yes, it absolutely handles state taxes. That's actually one area where I found it particularly helpful, since it flagged differences between federal and state rules for my business deductions. It helped me understand which expenses could be claimed on both returns versus just federal.

Wait, this actually works? I've tried calling the IRS before and gave up after being on hold for over an hour. How long did it take to get connected?

This sounds like a scam. No way they can get you through to the IRS faster than anyone else. The IRS phone system doesn't have special backdoors for third parties.

It absolutely works - I was connected in about 35 minutes instead of the hours I spent previously. They use technology to navigate the IRS phone tree and hold system, then call you when an agent is actually on the line. It's definitely not a scam. They don't have "backdoors" - they just have systems that handle the waiting and navigating for you. Think of it as paying someone to wait on hold so you don't have to. The IRS agent won't know you used a service to connect - you're just getting transferred to a live call once they reach a human.

That's a really good point I hadn't considered. I probably spent 15 hours last year just on my taxes, and that was before all these complications. Do you know if tax preparation fees are tax deductible?

Unfortunately, tax preparation fees aren't deductible for individuals anymore since the 2017 tax law changes. However, if you have a business (which you do with your craft sales), you can deduct the portion of tax prep fees related to your business on Schedule C. So if your tax preparer charges $400 and roughly 30% of your return complexity is from your business, you could deduct about $120 as a business expense. Make sure they break down their fee so you can document this properly!

This is terrible advice. I thought the same thing until I got audited last year. Turns out I'd been incorrectly handling my home office deduction for my side business for 3 years. Ended up owing $3,200 in back taxes plus penalties. A $400 tax pro would have saved me thousands.